Abstract
The title compound 4’,9’,4”,9”-tetra-tert-butyl-1’,6’,1”,6”-tetramethoxy-2,5-dithia[3.3] metabiphenylophane was synthesized as a calixarene like large-sized metacyclophane from the corresponding 3,3’-bis(chloromethyl)-5,5’-bis(1,1-dimethylethyl)-2,2’-dimethoxy-1,1’-biphenyl and 3,3’-bis (mercaptomethyl)-5,5’-bis(1,1-dimethylethyl)-2,2’-dimethoxy-1,1’-biphenyl via an intermolecular condensation reaction. The compound was characterized using 1H NMR spectroscopy and mass spectrometry. Its exact conformational structure was determined via single crystal X-ray diffraction analysis. The compound has quite strained 1,2-alternate like structure because of its two high dihedral angled and rigid biphenyl parts in the crystal. The crystal includes the two isomers as two different 1,2-alternate like conformers, and the ratio of the two isomers is 78:22.
Highlights
Calixarenes are cyclic compounds consisting of aromatic rings and methylene bridge chains
Calixarenes are considered as a member of the metacyclophane family [2] and readily prepared by using base-induced condensation of t-butylphenol and formaldehyde, their bridges limited to methyene groups
For the purpose of obtaining a wide variety of calixarene analogues, [1n] metacyclophanes containing oxygen [3] [4] or nitrogen [5] as a hetero atom rather than so1ely methylene groups in the bridges have been prepared. Cyclic compounds such as calixarenes and large sized metacyclophanes have various conformations derived from their orientations of the aromatic parts [6]
Summary
Calixarenes are cyclic compounds consisting of aromatic rings and methylene bridge chains. (2016) Synthesis and Crystal Structure Determination of 4’,9’,4”,9”-Tetra-t-Butyl-1’, 6’,1”,6”-Tetramethoxy-2,5-Dithia[3.3] Metabiphenylophane. For the purpose of obtaining a wide variety of calixarene analogues, [1n] metacyclophanes containing oxygen [3] [4] or nitrogen [5] as a hetero atom rather than so1ely methylene groups in the bridges have been prepared. Cyclic compounds such as calixarenes and large sized metacyclophanes have various conformations derived from their orientations of the aromatic parts [6]. As part of our ongoing research and continuous efforts towards the development of new materials, previously we reported the crystal structure of the several cyclophanes using an alternative synthetic pathway [7] and cesium ion template effect [8], but the large-sized metacyclophanes having ether bridges and biphenyl units have not been synthesized and reported. A crystal structure analysis is performed to determine the exact structure of the molecule
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